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Have you ever thought about why Chicago is the mecca of improv? Well, I recently had the chance to explore this question in depth when WBEZ, the public radio station in Chicago, contacted me about doing a story about it for their Curious City show.

If you ask me, Chicago really has all the right elements for making it the perfect destination for improv. I First of all, for a major city, Chicago is an affordable place to live on what an improviser makes at his or her temp job while taking classes and running around town doing shows.

Secondly, you have the history of improv here, plus so many different improv schools and performance opportunities, and of course, the genuineness of Chicagoans makes the people in the improv/acting community beyond supportive. Plus, there is a deep respect for craft here. There is no show business pressure here, so the stakes are fairly low, which makes it a great place to create, take risks and make lasting friendships.

In the story, however, we wanted to get some other people’s thoughts on why Chicago has become an important destination for improvisers, so I interviewed Susan Messing, TJ Jagodowski and Jonathan Pitts to get their thoughts on this as well.

What I’ve Learned After 50 Episodes of Improv Nerd

Next week we will be airing our 50th episode of Improv Nerd. It’s been less than two years since we started Improv Nerd, and recently I’ve been reflecting on how it all came about.

For more than ten years I was a contributor for WBEZ, a public radio station here in Chicago. I started out interviewing authors for their morning newscast, Eight Forty Eight, and then I got my own segment on the show called Studio 312, where I specialized in interviewing comedians and celebrities. I got to interview tons of comedy legends like Conan O’Brian, Shelley Berman, Harold Ramis, Adam McKay, Jeff Garlin, Tommy Chong, Robert Klein and, believe it or not, Cindy Crawford. The segment was popular, and I was doing something the station needed — making fun of public radio. I could tell by the response I’d get when I would run into a listener that I was doing something they really appreciated.

But after ten years, I wanted more exposure, a little more money, and most importantly, my own weekly radio show. It seemed only logical: I was already familiar with the station and popular with listeners. All we had to do was expand what we were already successfully doing to an hour-long show. So I set up a meeting with management.

I brought my friend Darryl, a former used car salesman, to act as my faux agent. We met in a windowless conference room and talked about the potential of making Studio 312 into a show. After several meetings, nothing came of it, nothing. I was devastated, and worse I was taking it personally. I was hurt, angry, disappointed, sad, and afraid my dreams of being the next Howard Stern were over. I would never be on the radio again, ever. I thought I had wasted all those years and achieved nothing. Absolutely nothing.

The problem was not WBEZ, it was thinking that WBEZ was the only way I could get a show.

As improvisers, we thrive on creating something from nothing. But sometimes we need to let go of the something we already have to create the nothing we need. Unfortunately, I work slowly, so it wasn’t until almost two years (and a lot of self-pity and self-hatred) later that I created Improv Nerd.

The idea was to create a live interview show that would be recorded for a podcast where I would interview legends of improv, then improvise and talk about what we just improvised. I would combine two things I was good at: interviewing people and improvising. As Jet Eveleth said to me the last time I gave her a ride home, “You are combining your passion with your passion.”

We put up the first season at Stage 773, and the hardest part was asking the guests. I think I wanted them to say no to being on the show more than I wanted them to say yes. I remember how terrified I was interviewing Dave Pasquesi and how much shame I felt asking Tim Meadows to be on the show.

We are now finishing our seventh season and have another season coming up in the fall. And people are listening. I’ve gotten emails from people as far away as Australia and Northern Ireland who’ve listened to the show. People who have asked for my autograph and invited me to come teach. People who have contacted me and told me that I’ve helped them.

I wish I could end this blog by saying I no longer want validation from famous institutions. I wish I could end by saying something like “This is a big world with lots of opportunities. I can shape my own destiny.” But that would not be entirely true. There is a part of me, a big part, who is still looking for someone else to validate me because I still don’t really value what I do. I still sometimes tell myself that Improv Nerd doesn’t matter, it’s just a silly podcast, and I’m not worth anything unless I am on a network sitcom or writing for Conan or co-staring in some big studio comedy this summer.

Yes, I am sad to say I am still waiting for my big break, some big name job that will help me finally start to feel like I’ve made it in comedy. And until that comes, the only advice I can give you is this: Continue to create, because I’ve found that nothing else makes the waiting more enjoyable.